3-Methoxybenzyl cyanide

Sodium amide 3-Methoxybenzyl cyanide Magnesium Ethyl bromide... 

Suggest a reasonable three step sequence showing all necessary reagents for the preparation of m methoxybenzyl cyanide from m methoxybenzaldehyde... 

Similar yields of substituted a-phenylcinnamonitriles can be obtained using p-methoxybenzyl cyanide and anisaldehyde, or benzyl cyanide and anisaldehyde... 

Displacement catalyst. In the preparation of p-methoxybenzyl cyanide from the chloride, a small amount of sodium iodide apparently functions as catalyst, although no evidence is presented that this is the case. ... 

R. B. Woodward was one of the leading organic chemists of the middle part of the twentieth century. Known primarily for his achievements in the synthesis of complex natural products, he was awarded the Nobel Prize in chemistry in 1965. He entered Massachusetts Institute of Technology as a 16-year-old freshman in 1933 and four years later was awarded the Ph.D. While a student there he carried out a synthesis of estrone, a female sex hormone. The early stages of Woodward s estrone synthesis required the conversion of ra-methoxybenzaldehyde to ra-methoxybenzyl cyanide, which was accomplished in three steps ... 

See Anisamino and under Salicylamine and m-Hydroxybenzylamine. p-Methoxybenzyl cyanide. 

Reticuline (38), one of the most important intermediates in the biosynthesis of opium alkaloids, has been synthesized in racemic form (Scheme 7) (78). 6-Methoxy-7-benzyloxyisoquinoline (39), prepared from O-benzylisovanillin via a modified Pomeranz-Fritsch isoquinoline synthesis, was treated with benzoyl chloride and potassium cyanide to obtain Reissert compound 40. Alkylation of the anion generated from 40 with 3-benzyloxy-4-methoxybenzyl chloride gave the corresponding 1-substituted Reissert compound 41 which was hydrolyzed in alkaline medium to 1-benzylisoquinoline derivative 42. Quatemarization of 42 with methyl iodide followed by sodium borohydride reduction and debenzylation led to ( )-reticuline (38) in about 25% overall yield from 39. 

Jackson et al. (22) reported the biomimetic total synthesis of ( )-cularine (67) itself (Scheme 11). Benzyolation of isoquinoline 68 in the presence of potassium cyanide gave Reissert compound 69, the anion of which was alkylated with 3-benzyloxy-4-methoxybenzyl chloride, resulting in intermediate 70. After al-... 

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